HATU
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HATU 속성
- 녹는점
- 183-188 °C (dec.)
- RTECS 번호
- XZ5633000
- 저장 조건
- 2-8°C
- 용해도
- >16mg/mL in DMSO
- 물리적 상태
- powder to crystaline
- 색상
- 흰색에서 거의 흰색
- 수용성
- 아세토니트릴에 용해됩니다. 물에 불용성.
- InChI
- InChI=1S/C10H15N6O.F6P/c1-13(2)10(14(3)4)15-8-6-5-7-11-9(8)16(17)12-15;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
- InChIKey
- KZAWCZZRROLLDL-UHFFFAOYSA-N
- SMILES
- [P+5]([F-])([F-])([F-])([F-])([F-])[F-].C(=[N+]1/N=N(=O)C2=NC=CC=C/12)(\N(C)C)/N(C)C
- CAS 데이터베이스
- 148893-10-1(CAS DataBase Reference)
안전
- 위험 및 안전 성명
- 위험 및 사전주의 사항 (GHS)
위험품 표기 | Xi,Xn,E | ||
---|---|---|---|
위험 카페고리 넘버 | 36/37/38-20/21/22-2 | ||
안전지침서 | 26-37/39-36/37-36-35 | ||
유엔번호(UN No.) | 1325 | ||
WGK 독일 | 3 | ||
F 고인화성물질 | 10-21 | ||
위험 등급 | 4.1 | ||
포장분류 | Ⅱ | ||
HS 번호 | 29339999 |
HATU C화학적 특성, 용도, 생산
개요
HATU, first prepared by Louis A. Carpino in 1993, is widely used in carboxylic acid amidation reactions. It acts as a facilitator of amide bond generation by activating the carboxyl group.화학적 성질
White crystalline to off-white powder용도
HATU[148893-10-1] is a coupling reagent and used as an additive in peptide synthesis. It is also involved efficiently to speed up the coupling process and reduces the loss of chiral integrity.Reagent for: Synthesis of Aurora A kinase inhibitors, HPLC assay to determine D- and L- acid enantiomers in human plasma, Amide bond formation reactions.
Catalyst for: Selective acylation, Selecocyclization-oxidation deselenation sequence.
화학 반응
HATU is a very promising coupling agent for chemical protein synthesis.![Cyclisation of ortho-, meta- and para-arylopeptoids](/NewsImg/2024-07-29/6385785946199084013901326.png)
This strategy was exploited to prepare macrocycles from the trimeric linear arylopeptoids (ortho-, meta-, and para-) containing isopropyl or ethyl side chains, synthesized as described by Hjelmgaard et al. The cyclization procedure reported for α,β-cyclopeptoids was applied. The linear arylopeptoids were cyclized in the presence of HATU and DIPEA in CH?Cl?/DMF (4:1) after the deprotection of the tert-butyl group in TFA/CH?Cl?.
![Macrocyclization of the linear trimer](/NewsImg/2024-07-29/6385785936811151488286583.png)
After the synthesis of the Fmoc-protected monomers, the oligomers were synthesized on the 2-chlorotrityl resin with excellent yield of coupling (>98%). The trimers and tetramers of the different isomers were synthesized in good overall yield (60-84%). Then, the crude oligomers were cyclized in DMF in the presence of HATU and DIPEA in high dilution (3 × 10?3 M) to furnish the cyclized trimers and tetramers in good yields ranging between 32% and 72%.
Synthesis
The synthesis of HATU is as follows:The resulting residue treated with 2-Methoxycarbonylamino-3-methyl-butyric acid (60 mg, 0.343 mmol) and HATU (130 mg, 0.343 mmol), suspended in DMF (3 mL) and cooled to 0° C. DIPEA (0.272 mL, 1.56 mmol) was added dropwise. After stirring for 4 h, NaOH (5M in H2O, 0.300 mL, 1.5 mmol) was added. This mixture was stirred for 3 h then diluted with EtOAc and washed with 1 M LiOH (2*) then brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude residue was then purified by HPLC to afford the title compound (53 mg, 44%).참고 문헌
[1] CHAWLA P A, SHOME A, JHA K T. Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium (HATU): A Unique Cross-Coupling Reagent[J]. SynOpen, 2023, 66 2: 0. DOI:10.1055/s-0042-1751499.[2] LOUIS A. CARPINO. Comparison of the Effects of 5- and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers?,?[J]. Organic Letters, 2000, 2 15: 2253-2256. DOI:10.1021/ol006013z.
HATU 준비 용품 및 원자재
원자재
준비 용품
HATU 공급 업체
글로벌( 677)공급 업체
공급자 | 전화 | 이메일 | 국가 | 제품 수 | 이점 |
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Allfluoro pharmaceutical co. ltd. | 021-26137118 +8615821363818 |
sales@allfluoro.com | China | 5791 | 58 |
Zhengzhou Anbu Chem Co.,Ltd | +86-0371-88006763; +8615988602810 |
sales@anbuchem.com | China | 3000 | 58 |
LEAP CHEM CO., LTD. | +86-852-30606658 |
market18@leapchem.com | China | 24738 | 58 |
Watson Biotechnology Co.,Ltd | +86-18186686046 +86-18186686046 |
sales01@watsonbiotech.cn | China | 5814 | 58 |
Wuhan Fortuna Chemical Co., Ltd | +86-027-59207850 |
info@fortunachem.com | China | 5984 | 58 |
Hebei Guanlang Biotechnology Co,.LTD | +86-19930503253; +8619930503252 |
daisy@crovellbio.com | China | 5838 | 58 |
Hebei Fengjia New Material Co., Ltd | +86-0311-87836622 +86-17333973358 |
sales06@hbduling.cn | China | 15695 | 58 |
Henan Bao Enluo International TradeCo.,LTD | +86-17331933971 +86-17331933971 |
deasea125996@gmail.com | China | 2503 | 58 |
Ouhuang Engineering Materials (Hubei) Co., Ltd | +86-86177 |
admin@hbouhuang.com | China | 2952 | 58 |
Hebei Zhuanglai Chemical Trading Co.,Ltd | +8613343047651 |
admin@zlchemi.com | China | 3002 | 58 |